In July, 2009, President Barack Obama unveiled the American Graduation Initiative, a 10-year; $12 billion plan to invest in Community Colleges, seen as crucial during the current challenging fiscal climate. The initiative aims to give Community Colleges resources needed to increase enrollment, graduation and jobs. There are 6 million students in Community Colleges. Obama's goal is to reach 5 million additional graduates by 2020. It is estimated that smoking prevalence in this population is 28 to 30%. The proposed study investigates Web- Assisted Tobacco Intervention (WATI), an effective intervention in need of more randomized trials, to meet the needs of this growing population of Community College students, who are an understudied and underserved population of young adult smokers, returning war veterans and persons re-entering the job market. The proposed study's 3 phases are: Phase 1, Key Informant Interviews and Focus Groups to first gain a better understanding of engagement (recruitment and retention), and the needs and characteristics of this unique population; Phase 2, a Group Randomized trial, comparing a reactive basic web-assisted tobacco intervention (with evidence-based components, but limited interactive features) to a proactive multi-faceted online intervention linking various novel WATI components: proactive texting, interactive features, and socially supportive online environments; and Phase 3, dissemination of cessation strategies to the scientific community and Community College stake-holders. The main advantage of the proposed study is that it assesses the effectiveness of recruitment, retention and cessation interventions in the contexts of 1) easily accessible web- based resources for Community College populations, and 2) novel targeted interactive web-site features that can inform interventions for the target population and other populations of adult smokers across large geographic regions. This proposal directly addresses research needs highlighted by the DHHS 2008 update of Clinical Practice Guidelines for Treating Tobacco Use and Dependence: low-income populations; young adult populations; and promising cessation interventions. We hope to learn which formats and interventions are effective in the web-based medium.